Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

Scholarly Works

• Bugden, F. E.; Westwood, J. L.; Stone, H.; Xu, Y.; Greenhalgh, M. Synthesis and applications of fluorinated, polyfluoroalkyl- and polyfluoroaryl-substituted 1,2,3-triazoles. Organic Chemistry Frontiers 2024, 11, 5938–5984. doi:10.1039/d4qo01334d
• Kong, F.; Zhang, R.; Wang, X.; Ni, C.; Hu, J. Facile double O-difluoromethylations of diphenols with TMSCF2Br. Tetrahedron Letters 2024, 155335. doi:10.1016/j.tetlet.2024.155335
• Petko, K. I.; Filatov, A. A.; Yagupolskii, Y. L. Multigram two-step synthesis of difluoromethyl ethers from aliphatic alcohols and glycols. Journal of Fluorine Chemistry 2024, 278, 110330. doi:10.1016/j.jfluchem.2024.110330
• Coe, M.; Bede, F.; Koch, C. J.; Espiritu, D. D.; Prakash, G. Synthesis of gem‑bromofluoroolefins using singlet bromofluorocarbene generated from ethyl dibromofluoroacetate via a Wittig-type reaction. Journal of Fluorine Chemistry 2024, 276, 110278. doi:10.1016/j.jfluchem.2024.110278
• Yang, J.; Li, M.; Tan, G.; Liu, F.; Qin, H. N‐Directed defluorinative γ‐C(sp3)−H allylation of sulfamate esters for synthesis of gem‐difluoroalkenes via photoredox catalysis. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400011
• Xie, Q.; Hu, J. A Journey of the Development of Privileged Difluorocarbene Reagents TMSCF2X (X = Br, F, Cl) for Organic Synthesis. Accounts of chemical research 2024, 57, 693–713. doi:10.1021/acs.accounts.3c00719
• Lin, D.; de Los Rios, J. P.; Surya Prakash, G. K. Photoredox Catalysis for the Synthesis of N-CF2 H Compounds Using 1-((N-(difluoromethyl)-4-methylphenyl)-sulfonamido)pyridin-1-ium Trifluoromethanesulfonate. Angewandte Chemie (International ed. in English) 2023, 62, e202304294. doi:10.1002/anie.202304294
• Lin, D.; de los Rios, J. P.; Surya Prakash, G. K. Photoredox Catalysis for the Synthesis of N‐CF2H Compounds Using 1‐((N‐(difluoromethyl)‐4‐methylphenyl)‐sulfonamido)pyridin‐1‐ium Trifluoromethanesulfonate. Angewandte Chemie 2023, 135. doi:10.1002/ange.202304294
• Kong, T.; Hu, J. Difluoromethyl 2-Pyridyl Sulfone: A Versatile Reagent for the Synthesis of Organofluorine Compounds. Perfluoroalkyl Substances; The Royal Society of Chemistry, 2022; pp 113–145. doi:10.1039/9781839167591-00113
• Jiang, B.; Zhang, S. Synthesis of Quinolines and 2‐Functionalized Quinolines by Difluorocarbene Incorporation. Advanced Synthesis & Catalysis 2022, 364, 2157–2162. doi:10.1002/adsc.202200263
• Xu, J.; Liu, J.; Chen, G.; Xiong, B.; Zhang, X.; Lian, Z. Palladium-catalysed difluoroolefination of benzyl tosylates toward the synthesis of gem-difluoro-2-trifluromethyl styrene derivatives. RSC advances 2022, 12, 12983–12987. doi:10.1039/d2ra02473j
• Xu, J.; Yang, C.; Dai, D.; Hou, W.; Xu, Y. Synthesis and Application of β‐Alkynyl‐γ,γ‐Difluoroallylboronates for Metal‐Free Allylation of Aldehydes in Water. Advanced Synthesis & Catalysis 2022, 364, 1228–1232. doi:10.1002/adsc.202200048
• Liu, A.; Ni, C.; Xie, Q.; Hu, J. TMSCF2 Br-Enabled Fluorination-Aminocarbonylation of Aldehydes: Modular Access to α-Fluoroamides. Angewandte Chemie (International ed. in English) 2021, 61, e202115467. doi:10.1002/anie.202115467
• Liu, A.; Ni, C.; Xie, Q.; Hu, J. TMSCF2Br‐Enabled Fluorination–Aminocarbonylation of Aldehydes: Modular Access to α‐Fluoroamides. Angewandte Chemie 2021, 134. doi:10.1002/ange.202115467
• Tu, J.-L.; Yang, J.-W.; Xu, W.; Su, M.; Liu, F. Amidyl radical-mediated aminodifluoroallylation of alkenes via photoredox catalysis. Organic Chemistry Frontiers 2021, 8, 6405–6410. doi:10.1039/d1qo01208h
• Fuchibe, K.; Yamada, A.; Hachinohe, K.; Matsumoto, K.; Takayama, R.; Ichikawa, J. Synthesis of Difluoroalkenes from Thiocarbonyl Compounds via Difluorothiiranes: Electrophilic Counterpart to Wittig-Type Difluoromethylidenation. Bulletin of the Chemical Society of Japan 2021, 94, 2451–2465. doi:10.1246/bcsj.20210248
• Martín-Heras, V.; Daniliuc, C. G.; Gilmour, R. An I(I)/I(III) Catalysis Route to the Heptafluoroisopropyl Group: A Privileged Module in Contemporary Agrochemistry. Synthesis 2021, 53, 4203–4212. doi:10.1055/a-1485-4916
• Yang, R.-Y.; Wang, H.; Xu, B. Base promoted gem-difluoroolefination of alkyl triflones. Chemical communications (Cambridge, England) 2021, 57, 4831–4834. doi:10.1039/d1cc01132d
• Chen, D.; Fan, Z.; Huang, L.; Gao, K.; Xiao, P.; Ni, C.; Hu, J. TMSCFX2 (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes. Chemical communications (Cambridge, England) 2021, 57, 319–322. doi:10.1039/d0cc06004f
• Ispizua-Rodriguez, X.; Barrett, C.; Krishamurti, V.; Prakash, G. K. S. Silicon-based difluoromethylations, difluoromethylenations, pentafluoroethylations, and related fluoroalkylations. The Curious World of Fluorinated Molecules; Elsevier, 2021; pp 117–218. doi:10.1016/b978-0-12-819874-2.00012-6

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